Cigar Aficionado sent Michael Kaplan to report a story about the hottest young online poker players. He came back with a great piece—which you can read in the August issue, on newsstands soon—and a desire to play the game well. Here, in three parts, is his experience.

Spend enough time with young guys making a ton of money playing poker online and a simple thought inevitably crosses your mind: How hard can it be? Especially if your goal isn't to earn $1,000 an hour, as online specialist Alan Sass does. No, let's say your goal is far more modest, perhaps a couple thousand a month. You're willing to put in the time, willing to learn, willing to lose a couple bucks and a lot of dignity in the process. In short, can a hack poker player, who's never played a single hand online, be transformed into a steady winner?

I pose this question to Sass himself, keeping it all in the second person (just in case he says no). But he figures that it shouldn't be a problem. He agrees to provide the kinds of lessons that'll turn me into a winning player. Cool.

But first I need to be properly equipped. After realizing that this is never going to work on my under-RAMmed Mac, I locate a reconditioned Windows computer for $500, put an additional $600 into a FullTilt.com poker account (I originally wanted to deposit $1,000, but the site prefers to take only $600) and spend a few days getting a computer program called Hold'em Manager up and running. This is a piece of software that tracks the play of opponents and gives you an idea as to how often they bluff, how hard it is to make them fold, how aggressive they tend to be under various conditions.

Ready to post blinds, I meet Sass in his Las Vegas apartment. He advises that we enter into a six-handed game (more action than nine-handed) and suggests that I play multiple tables. I demur on the latter (surely he thinks I'm a wussy), buy into a 25-cent/50-cent no-limit Texas Hold'em game for $50 (the maximum buy-in, which Sass says to always maintain) and start playing. Or at least I press the buttons. Initially, he's really the one doing the playing. He tells me when to three-bet ("most pairs in the blinds and out of position with connectors"), checking out players' stats on the software, advising me to bet on every street against passive opponents when facing a raggedy board. I absorb it all as best I can, but here is the biggest, broadest takeaway from my first session with Sass: measured aggression is key. Under his tutelage, I am raising with pre-flop hands that I would have previously folded (suited gap cards, such as, say, 6, 8 of diamonds). But he's also guiding me away from mediocre situations, after the flop, that would have cost me a lot of money.

We manage to piss off a couple of players who think I am incredibly lucky, put pressure on the big blinds, and show Herculean strength at appropriate moments. If we're in the hand, we almost always raise early on. That said, we promptly lose a buy-in of $50.

Major lesson: aggression can cost you money in the short run, but it pays off long-term.

Minor lesson: don't worry about losing if you're doing the right thing.

After an hour or so of noodling around, we're ahead $30. Not much, but not bad, relatively speaking. It's almost a buy-in. Even better, Sass acknowledges that I am not hopeless. He pretty much says that I can do this if I feel like it.